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Synthesis and X-ray crystal structure study of the hydroxyurea and hydantoin derivatives of L-valine

The novel hydroxyurea 5 derivative of L-valine was prepared by aminolysis of N-(1-benzotriazolecarbonyl)-L-valine cyclohexanemethylamide 4 with hydroxylamine. The corresponding hydantoin derivative 6 was synthesized by base catalyzed cyclization of the amide 4. The exact stereostructure of hydantoin derivative 6 has been determined by X-ray crystal structure analysis. The chiral atom of the hydantoin ring in 6 has S configuration what is in agreement with its configuration in the starting L-valine. The molecules of 6 are joined into infinite chains by N-H-O intermolecular hydrogen bond. The infinite chains are additionally linked by two C-H -O hydrogen bonds, thus forming two-dimensional network. The hydantoin derivative of L-valine 6 and its L-leucine analoque LH have similar packing arrangements, so they are homostructural.

hydantoin ; hydrogen- bonding ; hydroxyurea ; L-valine ; single crystal X-ray analysis

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